N, n&#39;-dioctadecyl-beta-amino-propionamide



Patented Sept. 2, 1947 p N,N'-DIOCTADECYL-BETA-AMINO- PROPIONAIWIDEKathryn L. Lynch, Stamford-Conn assignor to American Cyanamid Company,New York, N. Y., a corporation of Maine No Drawing. Continuation ofapplication Serial No. 472,386, January 14, 1943. This application filedSeptember 14, 1945, Serial No. 616,461

excellent softening agent for cotton cloth. Be-

cause of the cationic activity of its acid salts in aqueous solutions itis also useful in ore-dressing operations involving acidic typematerials.

In carrying out the reaction between the acrylic acid ester andoctadecylamine a. reaction temperature below about 150 C. and preferablybetween about 60 and 100 C. is employed. Two mols of the octadecylamineare preferably reacted with 1 mol of the lower alkyl ester of acrylicacid, such as methyl or ethyl acrylate, the reaction being continueduntil the conversion to the amide is substantially complete.

The following example is illustrative of a representative method for thepreparation of the compound of the invention:

Example 265 g. (1 mol) of octadecylamine is melted and held at 6 4 C.while adding thereto 43 g. (0.5 mol) of methyl acrylate over a periodof30 minutes. Heat is applied and the mixture kept at 65 to 70 C. withagitation. Samples are taken from the reaction mixture from time to timeand analyzed to show the progress of the reaction. The results are shownin the following table:

Time of Conversion Heating tothe Amide Temperature Hours Per unit C.

7 78 Raised to 93 10 90 90-95 90-95 1 Claim. (Cl. 260-561) 2 287 g.-of asoft waxy product is obtained after the removal of methanol bydistillation. The product, N,N-dioctadecyl p amino propionamide, isdispersible in hot dilute acid to give 5 surface-active solutions. Whenapplied to cotton and rayon cloth excellent softening effects areattained.

The product may be-dissolved in aqueous formaldehyde by adding 49 g. ofit to 52 cc. of 40% 10 formaline and diluting with 200 cc. of warmwater. The thin creamy paste may be diluted with water if desired. Thismixture also gives excellent softening when applied to cotton cloth.

This is a continuation of my copending appli- 16 cation Serial No.472,386 filed Jan. 14, 1943 which has become abandoned.

What I claim is: N,N -dioctadecyl-;3-amino-propionamide.

K20 KATHRYN L. LYNCH.

REFERENCES CITED 1 The following references are of record in the g5 fileof this patent:

UNITED STATES PATENTS OTHER REFERENCES Braun et al., "Ber. Deut. Chem.,vol. 60 1927), pp. 347-354.

Dermer et al., "J. Org. Chem., vol 8 (1943) p. 1'70.

Moi-sch in Chemical Abstracts. vol. 28 (1934) v pp. 2679 and 2680.(Abstract of Monatsh, vol. 63 45 (1933), p 220-235).

